ChemicalBook CAS DataBase List 2-Chloro-3-methoxypyridine

2-Chloro-3-methoxypyridine synthesis

7synthesis methods

Product Name:2-Chloro-3-methoxypyridine
CAS Number:52605-96-6
Molecular formula:C6H6ClNO
Molecular Weight:143.57

6636-78-8

74-88-4

52605-96-6

Step 1: 2-Chloro-3-hydroxypyridine (2.59 g, 20 mmol), iodomethane (2.98 g, 21 mmol) and potassium carbonate (K2CO3, 5.52 g, 40 mmol) were added to N,N-dimethylformamide (DMF, 50 mL). The reaction mixture was stirred at 60 °C for 4 hours. After completion of the reaction, it was cooled to room temperature and the mixture was poured into water and extracted with ethyl acetate. The organic phases were combined, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 2-chloro-3-methoxypyridine (2.58 g, 90% yield). Mass spectrum (ESI) m/z: 144.0 [M + H]+.

6636-78-8 Synthesis

6636-78-8
431 suppliers
$5.00/1g

74-88-4
349 suppliers
$15.00/10g

52605-96-6
187 suppliers
$6.00/250mg

Yield:52605-96-6 100%

Reaction Conditions:

Stage #1:2-chloro-3-hydroxypyridine with sodium methylate in N,N-dimethyl-formamide at 20; for 0.333333 h;
Stage #2:methyl iodide in N,N-dimethyl-formamide at 20; for 0.666667 h;Cooling with ice;

Steps:

1.1 step 1:
To a three-necked flask were added 2-chloro-3-hydroxypyridine (5.0 g, 39.0 mmol), N, N- dimethylformamide (60 mL); sodium methoxide (2.30 g, 43.0 mmol ). The reaction was stirred at room temperature for 20 minutes. Methyl iodide (8.20 g, 58.0 mmol) was added to the ice bath and stirred at room temperature for 40 minutes. Water (120 mL) was added and extracted with ethyl acetate (100 mL x 3); the organic phases were combined, washed with water (100 mL x 2) and brine (100 mL), dried over sodium sulphate and filtered. The filtrate was spin-dried to give a yellow liquid, compound 1 (5.58 g, 39.0 mmol, 100%) which was used directly in the next reaction;

References:

Kanghua (Shanghai) Drug Discovery Co., Ltd.;Ma Jingxiang CN107286084, 2017, A Location in patent:Paragraph 0008

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74-88-4
349 suppliers
$15.00/10g

52605-96-6
187 suppliers
$6.00/250mg

References